


The Pizza Man and The Babysitter

by werenotthelosechesters



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Babysitter Dean, Bottom Dean, Candles, Castiel's Tie, Frottage, M/M, Making Out, Netflix and Chill, Openly Bisexual Dean, Pizza Man Castiel, Power Outage, Rimming, Socially Awkward Castiel, Top Castiel
Language: English
Status: Completed
Published: 2015-10-16
Updated: 2015-10-16
Packaged: 2018-04-26 16:10:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,007
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5011177
Author URL: https://archiveofourown.org/users/werenotthelosechesters/pseuds/werenotthelosechesters
Summary: <blockquote class="userstuff">
              <p>Dean is babysitting Ben with Sam, but when they leave for the night he makes other plans. Until the doorbell rings and a handsome stranger brings him the pizza he'd forgotten they'd ordered. This is going to turn out to be a much better night than he expected.</p>
            </blockquote>





	1. Saved by the Doorbell

"Okay, man. Put the AC/DC hoodie on, Sam's gonna bring you to the park to play catch for a while." Dean tosses the shirt to Ben, who nods his head and puts his shoes on. Sam zips up his own jacket and waits for Ben to finish getting ready before they both run outside and into Sam's car to head to the park. Dean watches them drive off with a smile on his face. Ben is his best friend Lisa's son, but he reminds him so much of himself, even at eight years old that he could have sworn he was the product of the one night he and Lisa had spent together.

Dean likes to babysit Ben as often as he can when he isn't working at Singer's Auto as a mechanic, he figures it's good practice for when he has kids of his own and really, Ben is just a really cool kid. Since Sam will be gone for about a half an hour, Dean grabs a beer from the fridge and plops down on the couch to finish watching the episode of _Dr. Sexy, M.D._ he'd started earlier that day. Less than five minutes in, Dean has his feet up on the coffee table and his phone vibrates in his pocket. He unlocks his phone to discover a text from Sam.

**Sam- Hey, Jess is at the park with her little sister. She asked if I wanted to go with her to bring the kids to the arcade for supper.**

**Dean- You better say yes, you've only been in love with her forever.**

**Sam- I'm not in love with her -.- but Ben and I are gonna go, I'll text Lisa to let her know I'll drop him off on my way home.**

Dean smirks at that, Sam's been hung up on Jess since he'd first laid eyes on her.

**Dean- Don't do anything I wouldn't do ;)**

**Sam- Don't be gross. -.- See you tomorrow at Bobby's.**

And with that, Dean finds himself with the rest of the night ahead of him. Since it's a Friday, he figures it's as good a night as any to go get some dinner then head to a bar to pick someone up, probably a guy tonight, since watching _Dr. Sexy_ always put him in that state of mind. He hops off the couch and heads to take a quick shower. It doesn't take him long to get ready, he throws on some tight fitting jeans and a green button-down. He always feels out of place when he goes to the more posh clubs in the city, but these clothes have never failed him. Guys usually stare at his ass and compliment his eyes almost as soon as he walks in.

Just as he's looking in the mirror and squeezing some gel into his hand, the doorbell rings. He takes the stairs two at a time and is still running fingers through his hair as he opens the door to find a stranger standing on his front step. The man is gorgeous with a messy head of dark brown hair, blue eyes and just the right amount of stubble. Dean looks him up and down. The guy is wearing black slacks with a white button down shirt, a backwards blue tie, a rumpled trench coat and a Gabriel's pizza hat. The guy is also holding a pizza box with his name written on the ticket in black Sharpie.

"Ah, shit. I forgot we ordered a pizza." Dean muttered to himself. "Come on in, man. It's kind of cold out there." The man steps into the house and closes the door behind him. Dean walks into the kitchen and grabs a twenty dollar bill from the jar on top of his fridge. Gabriel's is the Winchesters' favourite pizza joint, they'd been ordering their usual pepperoni, sausage and green pepper pizza since they'd opened nearly two years ago. This delivery guy must be new, though, or else Dean would have ordered pizza way more often.

"So, uh..." Dean clears his throat, "Did Gabe finally decide to cut the goofy yellow uniforms or do you moonlight as an accountant?" Dean shoots a smile his way, hoping he's coming off as charming instead of mocking. The guy doesn't seem offended, he merely squints his eyes a little and Dean's smile spreads involuntarily. When he looks up, the guy catches his eye and Dean finds it impossible to look away.

"No, my name is Castiel, I'm Gabriel's brother. I stopped by the restaurant on my way home from work and he said he was running behind on orders, so he asked me to bring this to you." Castiel props up the pizza to accentuate is point. His voice is rough and low, and Dean thinks of a few obscene words he wouldn't mind hearing in that voice, particularly his name being moaned while Cas-

"Well, I guess it's my lucky night, then." Dean winks at Castiel and Cas cocks his head to the side. Dean doesn't think Cas could get any more adorable. "Yes, I suppose you would have been disappointed if you'd had to wait another hour for your order to arrive." Castiel looks down at the floor and Dean shuffles awkwardly. He wants to get to know this guy better, should he give him his number?

While Dean is caught up in his thoughts, Castiel is giving Dean a once-over. Cas' eyes are drawn to the man's slim hips and the way his shirt is stretched over the expanse of his chest and broad shoulders. He'd never been attracted to someone so quickly before, and just as Cas was admiring Dean's freckles and making his way back to his eyes, Dean looks up again. Cas curses his social awkwardness, wishes he were able to more easily read what people are thinking.

He clears his throat. "So, uh... Gabriel said to let you know this one's "on the house", to thank you for your continued patronage."Cas hands the box to Dean, who takes it with a smile. "Man, I've never been known to refuse a free pie, that's awesome. I'll call Gabe tomorrow to thank him." Cas smooths the wrinkles on the front of his jacket, not wanting to leave just yet. Dean fidgets a bit and takes a small step backwards.

"You know, there's lots of extra food here. We could hang out and watch some Netflix if you uh... if you don't have any other plans..." Castiel is trying to catch Dean's eye, but Dean seems intent on looking anywhere but directly at him. Dean is inviting him to have dinner with him. That's a good sign. Castiel couldn't think of anything he'd rather do.

"Dean..." Castiel notices the way his cheeks redden at the sound of his name, but Dean's eyes finally snap to his own and Castiel finds himself rethinking his favourite color. "I have no other plans, and I would enjoy spending the evening here." Dean's smile makes the skin around his eyes crinkle and all the tension bleeds out of his shoulders. He nods his head inside so Cas knows to follow him, then he heads into the kitchen.

After taking his shoes off, Castiel follows behind and is greeted by the sight of Dean Winchester bent at the waist reaching for something on the bottom shelf of his fridge. His legs are spread slightly and his jeans fit snugly so that the curve of his ass is on display. "Do you want a beer, Cas? Or I have Dr. Pepper or iced tea, if you want." Cas is finding it hard to answer, and when Dean looks over at him without standing up he raises an eyebrow while smirking at Cas' expression. "Cas?"

"Yes, a beer would be fine, Dean." Castiel blinks a few times. Dean takes his time grabbing the bottles and something from the top shelf and when he finally straightens up, he holds out a white bottle and asks "You ever try ranch dressing on your pizza?" Cas shakes his head no, but he'd be willing to try it. Dean balances the items on the pizza box and Cas follows him into the living room.

"You wanna take that coat off Cas, or are you cold?" Castiel smiles at him and shrugs out of the sleeves and throws it over the chair. He feels comfortable in Dean's home and he takes a seat on the couch where he hoped wouldn't be too far from where Dean decides to sit.

Dean sprawls out on the couch beside him and reaches over Castiel to the arm of the couch where the remote is sitting. Cas holds his breath and wills himself not to reach out to touch him. The body heat from Dean's chest is warming Cas from the inside out, and he now feels a little feverish. When Dean gets back into his seat, he glances at Castiel and he's unable to look away as he rolls up the sleeves of his button down to reveal his forearms. Dean opens the pizza box and both men take a slice as Dean begins browsing titles.

"Let me know when you see something you wanna watch, kay?" Cas nods his head and watches Dean as he takes his first bite of pizza. He groans around the bite and when he pulls away, he runs his tongue over his lips that glisten from the greasy food. Cas' mouth feels dry and he gives a little cough then reaches for his beer. Dean is trying to kill him, he's sure.


	2. Friday Night Lights

"Okay, try this" Dean takes Castiel's pizza-holding hand in his, and squirts a little bit of the ranch dressing on the edge of his pizza. Castiel smiles at him, they'd been purposefully making 'accidental' contact with each other for the last fifteen minutes, and Cas feels his heart start beating more quickly with Dean's hand wrapped around his. The movie playing in the background is just a formality at this point, both of them are wrapped up in the chemistry and tension in the room.

Cas raises the slice to his lips, aware of how intently Dean's eyes are focused on his mouth. He takes a purposefully slow bite and licks his lips while looking into Dean's green eyes. He hardly tastes the pizza, not as hungry as he thought himself to be. Dean looks at him expectantly, and Cas smiles, nodding his head. The victorious smile that wins is a prize in itself. Honestly Cas couldn't care less about the pizza anymore. 

When Cas puts the slice back down in the box, all of a sudden the lights go out and the movie stops playing. "Son of a bitch!" Dean's not ready for the night to end, he hasn't made his move yet and he no longer has the pretense of a movie to keep Cas around. He hears a chuckle in the dark, and suddenly realizes how loud the rain is against the window. "When did it start raining?"

Apparently Dean wasn't the only one who was distracted, because the only answer he gets is "It's raining?" He laughs at that, then tries to remember if he has a flashlight around. He finds one in the coffee table drawer but it isn't working and he's out of batteries. "I think I have some candles in my room, I'll be right back." Dean's face heats up as he mentions his bedroom and he's glad for the privacy the darkness provides. 

He tries to put his hand on the couch to push himself up, but winds up with a hand on Cas' thigh, which pulls a gasp out of the other man. Instead of moving it, he leans in closer until he feels a hot breath against his skin. Then a flash of lightning lights up the room and Dean remembers himself, pushing away and heading to his room to find the candles. 

His thoughts are racing. He's frustrated with himself for not manning up and making a move. He really wanted to feel Cas' lips against his. As he opens his bedroom door, he moves towards his closet and in the process manages to knock over a box full of books off his dresser. The loud crash prompts heavy, quickly-paced footsteps coming from down the hall. "Dean, are you alright?"

"Yeah, Cas. I just knocked some shit off my dresser, it's fine." Another strike of lightning exposes the worried look on Cas' face. Dean turns back to his closet and pulls out a box of candles. He places them on the dresser and kneels down to pick up the books. Castiel moves beside him and lights a candle with a lighter from his pocket. When he kneels down beside Dean to help pick up the books, he smiles sideways at him. "I figured it would be easier with a bit of light."

Cas can't seem to look away from Dean's eyes. The way the candlelight is hitting them makes them sparkle, and for the first time in his life he uses the word 'breathtaking' to mentally describe someone. Cas looks down at the other man's lips, wondering if they're as soft as they look. He runs his tongue over his own dry lips then looks back up to Dean's eyes, which seem darker now. He's leaning into Cas' personal space until their lips meet. Their first kiss is soft, slow and exploratory. When they break for air, Dean doesn't pull away, instead resting his forehead against Cas'. "Was that okay?"

"Of course, Dean." When they break apart, Dean stands up, then extends his hand to help Castiel to his feet. As they stand in the dim light, neither of them pull their hand away and Cas pulls Dean's body against his own. Dean's breath catches in his throat. Cas holds his hand more tightly and presses his lips back onto Dean's, satisfied by the way Dean melts into him. When they finally pull apart, Dean takes a small step backwards and pulls a lighter out of the box with the candles. 

Castiel watches with amusement as Dean lights the rest of the candles and places them on the dresser. The whole room is aglow with a soft light now and Cas is silently thanking God for the storm. When Dean turns back to him, he feels a bubble of nervous energy in the pit of his stomach. Dean seems completely at ease, though. Cas follows him closer to the center of the room and his mind goes blank when Dean grabs him by the tie and pulls him into another kiss.

This one is less gentle, and Cas finds himself gaining more confidence as his need for the man pressed against him grows. He moves his hand up to run fingers through short sandy hair. When he fists his hand through the strands to pull him closer, Dean sighs into his mouth. Cas runs his hands over Dean's shoulders, marveling at the taut muscles he feels rolling as Dean moves his hands up to Cas' first button on his shirt. He pops a few of them open the resumes kissing into Cas' mouth with an urgency that wasn't there before. Dean savors the anticipation of revealing more of Cas' skin.

Cas moves his hands down around Dean's waist to hold their bodies together. The heat between them would be uncomfortable if it didn't feel so damn good. Cas sucks Dean's bottom lip into his mouth then slowly releases it through his teeth. Dean's breathing more heavily now, and Cas can feel his heartbeat in his ears. Cas moves his mouth down to Dean's neck and relishes the feeling of Dean's stubble scratching against his own. That never fails to turn him on. As Cas gently sucks on Dean's neck, he's rewarded by a long groan from the back of Dean's throat.

Dean pushes his hips forward and Castiel gasps as he feels Dean's clothed erection grind against his own. The pair continue to kiss passionately, and Dean brings his hands back up to finish unbuttoning Cas' shirt. When he finally pushes it off the man's shoulders, his hands move to explore the newly exposed skin of their own accord. Cas' muscles are lean and long, and when he moves his hands down Castiel's abdomen, he shudders. Cas hurries himself to unbutton Dean's shirt, desperate to feel Dean's skin against his own. 

"Nice tattoo." Cas smirks up at Dean who laughs, "Thanks..." Dean moves away from Castiel to sit on his bed. Cas watches him with a smile until Dean reaches out to grab him by the tie and pull him down on top of him. Castiel props himself up on top of Dean, his arms on either side of the man's body. Castiel works on Dean's neck as Dean grinds upwards, seeking the friction he craves. Just as he breathes out a sigh of frustration, Cas lowers his hips against Dean's and earns a loud moan from his lover.

Cas looks into Dean's eyes as he repetitively moves his hips in time with Dean's breaths. Dean hasn't felt this turned on with his pants on since he was a teenager, so in a breathy voice, he tries to remedy the situation. "Cas... I need... we're wearing too many clothes." Cas slides down his body and effortlessly pops open the fly on Dean's jeans.


	3. Stay

"These jeans have been making me crazy all night. You have a fantastic ass." Dean rumbles a laugh at that, a sound that is quickly becoming one of Cas' favourite things in the world. Dean gasps when Castiel roughly pulls his jeans down his legs, and a little bit of precum soaks through the fabric of his black boxer briefs. 

Cas bends down and mouths at the wet fabric, then sneaks his hands under the waistband to pull them off and toss them to the floor. Castiel takes Dean into his hand and glances up to make eye contact with Dean as he lowers his mouth over the head of his cock. Dean moans and the sound encourages Cas to continue with his ministrations. 

He sinks down a little lower onto Dean's shaft, then bobs back up to run his tongue along the crown, causing Dean to twist his fingers into the blanket in an effort to keep himself grounded. Cas moves his right hand to massage Dean's balls as he takes more of Dean into his mouth. Dean groans when the head of his cock hits the back of Cas' throat. When Cas slowly makes his way back up to the tip, he licks Dean's slit, which causes Dean to swear. 

"Cas, fuck. This is... fuck. I need you to prep me. Condoms and lube are in the nightstand." Dean is surprised he'd been able to form a coherent sentence, after learning first-hand how good Cas is with his mouth. It didn't take long to find what he needed, and he got on his knees between Dean's legs. "Spread you legs wider, Dean..." 

Dean does as he's told, and feels uncomfortably exposed until his eyes lock with Castiel's and he sees the hunger with which the man is looking down at him. Cas bends down and teases Dean's sensitive ring of muscle with his finger covered in saliva. Dean's bucking towards him, and Cas takes his finger away, which causes Dean to growl. The sound goes straight to Castiel's dick and he's even more driven now than he was before to lean down between Dean's legs and flick his tongue over Dean's rim. Dean's eyes fly open in surprise, and he doesn't think it's possible to be this turned on.

Cas continues licking for a short while, then opens the bottle of lube and warms some in his hand before coating his finger with it and rubbing his finger tip in small circles over Dean's hole. Dean is moving his hips impatiently now, so Cas slides his finger inside and slowly moves it in and out. When Dean continues moving his hips to the rhythm, Cas pushes another finger inside and massages Dean's inner walls as Dean's breathing is coming in short, shallow pants.

Cas curls his fingers upwards until he finds Dean's prostate, which gets him a "Fuck, Cas. I need you inside me." Cas wants to feel Dean's heat wrapped around his cock, but he knows Dean isn't stretched enough to take it comfortably. Cas scissors his fingers to stretch Dean out a little more and when he starts fucking him with a third finger, Dean bucks his hips up as another small dribble of precum leaks out of the head of his cock. He tries to reach for Cas' belt. "Why are you still wearing clothes?"

Cas removes his fingers and Dean sits up, roughly undoing Cas' belt buckle and unzipping the fly, reaching his hand in to gently squeeze Cas' cock, resulting in a throaty groan from the blue-eyed man. Cas lets Dean pull his pants around his thighs and he kicks them off. Dean admires the sharp lines of Cas' hipbones and the lines they create that lead his eyes to his engorged, deep pink member. 

Dean reaches beside him on the bed and opens the wrapper of a condom, pinching the tip and rolling it over Castiel. Cas squirts some lube in his hand and lets it warm up before sliding his hand up and down his cock a few times. Dean's mouth waters and he wants Cas in his mouth, but he doubts either of them will last that long, so he contents himself with moving onto his hands and knees and spreading his legs. "No, please, Dean. I need to see you."

Dean is surprised, usually guys want him with his ass in the air, but he rolls onto his back and looks into Castiel's eyes as he teases at his entrance then pushes past his sensitive ring. Castiel is big, and even though he'd been properly stretched, he feels a pleasant burn as Cas bottoms out inside him. Cas' eyes are fixed on his own, and Dean has the distinct feeling that Cas is looking into his soul, yet he can't bring himself to look away.

Dean starts to move as he grows more comfortable, and soon Cas gets the message that Dean needs to get fucked. So Cas picks up the pace a little, grinding his hips into the other man's, caught up in giving and receiving the pleasure they both need. Cas' whole body is pressed closely to Dean, and his thrusts are small but deep, and soon he begins hitting Dean's prostate on each stroke. 

Their skin is hot and sweaty where they touch, their breath heavy and hot against each other's necks. Dean grabs at Cas' shoulders to brace himself and Cas continues his relentless pace. The tension in Dean's abdomen coils tightly, and the friction on his cock between his and Cas' bodies becomes too much when combined with the next thrust reaching the sweet spot inside him. Dean shouts Cas' name as he shoots his load onto Cas' chest. 

When Dean reaches his orgasm, his muscles clench tightly around Cas' cock, and the way Dean shouts his name is more than enough to send Castiel over the edge as his muscles tense and he spills his load inside Dean. Neither of them move for a little while, basking in the afterglow until Castiel pulls out, ties off the condom and shoots it into the small garbage can by Dean's bed. Dean uses a tissue to wipe off Cas' chest then discards it and pulls Castiel in close. 

At some point during the night, the storm must have stopped, because they can hear the movie playing quietly in the other room. Neither of them want to move, and Dean pulls Cas in closer, leaning in for a soft kiss before covering them both with the blanket.

"Cas?" Dean sounds tentative.

"Hmm?"

"Stay the night?" 

"Of course, Dean."

**Author's Note:**

> Hey guys, please don't hesitate to let me know if you notice and spelling or grammatical errors.


End file.
